4546-19-4Relevant academic research and scientific papers
Novel application of simple molybdates: Catalytic hydrolysis of an organophosphate neurotoxin under mild aqueous conditions
Kuo, Louis Y.,Dill, Kristina M.,Shari'ati, Yusef A.,Bright, Emily K.,McCormick, Theresa
, p. 1 - 7 (2017)
A novel protocol for hydrolyzing phosphonothioate neurotoxins has been developed that uses a readily available, inexpensive and non-toxic molybdate (MoO42?). The target organophosphate is O,S-diethylphenyl phosphonothioate (1), a mod
Selective hydrolysis of phosphorus(v) compounds to form organophosphorus monoacids
Ash, Jeffrey,Cordero, Paula,Huang, Hai,Kang, Jun Yong
, p. 6007 - 6014 (2021/07/21)
An azide and transition metal-free method for the synthesis of elusive phosphonic, phosphinic, and phosphoric monoacids has been developed. Inert pentavalent P(v)-compounds (phosphonate, phosphinate, and phosphate) are activated by triflate anhydride (Tf2O)/pyridine system to form a highly reactive phosphoryl pyridinium intermediate that undergoes nucleophilic substitution with H2O to selectively deprotect one alkoxy group and form organophosphorus monoacids.
METHOD FOR PRODUCING PHOSPHOESTER COMPOUND
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Paragraph 0023; 0029-0031, (2021/09/27)
PROBLEM TO BE SOLVED: To provide a method whereby, a phosphate compound selected from the group consisting of orthophosphoric acid, phosphonic acid, phosphinic acid, and anhydrides of them is used as raw material and, by one stage reaction, a corresponding phosphoester compound is produced. SOLUTION: To an aqueous solution of a phosphate compound, added is an organic silane or siloxane compound having an alkoxy group or an aryloxy group, and the mixture is subjected to a heating reaction, thereby producing a corresponding phosphoester compound without requiring a catalyst. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT
Selective esterification of phosphonic acids
Brodzka, Anna,Koszelewski, Dominik,Ostaszewski, Ryszard,Trzepizur, Damian
, (2021/09/27)
Here, we report straightforward and selective synthetic procedures for mono-and diesteri-fication of phosphonic acids. A series of alkoxy group donors were studied and triethyl orthoacetate was found to be the best reagent as well as a solvent for the performed transformations. An important temperature effect on the reaction course was discovered. Depending on the reaction temperature, mono-or diethyl esters of phosphonic acid were obtained exclusively with decent yields. The sub-strate scope of the proposed methodology was verified on aromatic as well as aliphatic phosphonic acids. The designed method can be successfully applied for small-and large-scale experiments without significant loss of selectivity or reaction yield. Several devoted experiments were performed to give insight into the reaction mechanism. At 30?C, monoesters are formed via an intermediate (1,1-diethoxyethyl ester of phosphonic acid). At higher temperatures, similar intermediate forms give diesters or stable and detectable pyrophosphonates which were also consumed to give diesters.31P NMR spectroscopy was used to assign the structure of pyrophosphonate as well as to monitor the reaction course. No need for additional reagents and good accessibility and straightforward purification are the important aspects of the developed protocols.
B(C6F5)3-catalyzed O-H insertion reactions of diazoalkanes with phosphinic acids
Jiang, Jun,Zhang, Xinzhi,Zhang, Yangyang,Zhao, Jincheng
supporting information, p. 5772 - 5776 (2021/07/12)
A highly efficient base-, metal-, and oxidant-free catalytic O-H insertion reaction of diazoalkanes and phosphinic acids in the presence of B(C6F5)3has been developed. This powerful methodology provides a green approach towards the synthesis of a broad spectrum of α-phosphoryloxy carbonyl compounds with good to excellent yields (up to 99% yield). The protocol features the advantages of operational simplicity, high atom economy, practicality, easy scalability and environmental friendliness.
Synthesis of phosphonates from phenylphosphonic acid and its monoesters
Henyecz, Réka,Kiss, Adrienn,Mórocz, Virág,Kiss, Nóra Zsuzsa,Keglevich, Gy?rgy
supporting information, p. 2642 - 2650 (2019/08/08)
Possibilities for the mono- and diesterification of phenylphosphonic acid were evaluated considering the microwave(MW)-assisted direct esterification, and the alkylating esterification. It was found that regarding the monoesterification, the reaction with 15-fold alcohol excess in the presence of [bmim][BF4] additive utilizing MWs is superior than the approach by alkylation. At the same time, for the conversion of the monoester intermediate to the diester, the reaction with alkyl halides in the presence of triethylamine as the base, again under MW irradiation, was found to be the method of choice. Phosphonates with both identical and different alkoxy groups were made available.
Cu(II)/Proline-Catalyzed Reductive Coupling of Sulfuryl Chloride and P(O)-H for P-S-C Bond Formation
Zhang, Xinghua,Wang, Dungai,An, Duo,Han, Boshi,Song, Xiang,Li, Liang,Zhang, Gaoqi,Wang, Lixian
supporting information, p. 1532 - 1537 (2018/02/10)
A considerably improved method for the Cu-catalyzed coupling of sulfuryl chloride with P(O)-H was described. Using commercially available l-proline as the ligand decreased the precatalyst loading, broadened the substrate scope and greatly promoted the efficiency of the coupling reaction. Moreover, gram-scale preparation, easy-to handle and recyclable catalyst featured this transformation.
Phosphonamide pyrabactin analogues as abscisic acid agonists
Van Overtveldt,Heugebaert,Verstraeten,Geelen,Stevens
, p. 5260 - 5264 (2015/05/13)
A four step synthesis towards novel phosphonic pyrabactin analogues is presented. Via a stomatal closure and germination assay, the ability of the analogues to selectively induce the ABA-signaling pathway was demonstrated.
Phosphinate ruthenium complexes
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Page/Page column 56; 57, (2015/09/23)
Provided herein are ruthenium complexes of Formula I, and processes of preparation thereof. Also provided are methods of their use as a metathesis catalyst.
Phosphonothioate hydrolysis by molybdocene dichlorides: Importance of metal interaction with the sulfur of the thiolate leaving group
Kuo, Louis Y.,Baker, Devon C.,Dortignacq, Adria K.,Dill, Kristina M.
, p. 4759 - 4765 (2013/09/24)
The metallocene bis(cyclopentadienyl)molybdenum(IV) dichloride Cp 2MoCl2 hydrolyzes O,S-diethyl phenylphosphonothioate (1) with only P-S scission to yield a phosphonate under mild aqueous conditions. In terms of degrading phosphonoth
